


You Know What It's Paved With And You Know Where It's Going

by Chaz_1789



Series: Rules Meant To Be Broken [5]
Category: Supernatural
Genre: Alternate Universe - High School, Angst and Fluff, Dean POV, Destiel - Freeform, High School Student Castiel, High School Student Dean Winchester, Implied/Referenced Alcohol Abuse/Alcoholism, Implied/Referenced Child Abuse, John Winchester's A+ Parenting, M/M, References to Neglect, Sex Worker Castiel, they're both seventeen
Language: English
Status: Completed
Published: 2018-08-02
Updated: 2018-08-02
Packaged: 2019-06-20 19:05:22
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,755
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15540963
Author URL: https://archiveofourown.org/users/Chaz_1789/pseuds/Chaz_1789
Summary: On the slippery slope of trying to be helpful, Dean may just be reaching terminal velocity.





	You Know What It's Paved With And You Know Where It's Going

**Author's Note:**

> You'll definitely need the backstory by this point, so go and enjoy parts 1-4 if you haven't already!

Running on about forty five minutes of sleep, this seemed like a good idea. Dean was aware that might not still be the case later after a solid eight hours, but right now, it was the best idea. It was his only idea.

He knew damn well it wasn't his place to do this. It wasn't. He didn't owe Cas anything, although an argument could be made that he owed him for services rendered, but he didn't think Cas would take the money no matter how much he needed to pay rent. And wasn't that just the kicker; Cas wouldn't take money he'd earned fair and square...because he liked Dean.

As for Dean, well, he couldn't get Cas out of his head. They just seemed to orbit each other; no matter the fucking odds, no matter that it was a bad idea, no matter that neither of them planned it, they just ended up falling back into each other. And after seeing how Cas was living, after meeting his adorable little sister, after finding out just how far gone his mom was, Dean was determined to do something, _anything_ he could to help. Especially if Cas wouldn't accept his money.

Thinking back on the tougher times of his own life during the sleepless night, Dean'd had an epiphany.

Bobby.

Bobby would understand.

Bobby was one guy with a sturdy as fuck moral compass and who never stood for any crap from anyone, not even John Winchester (and a _lot_ of crap could come from John Winchester). Dean trusted him. It was hard not to trust a guy who'd willingly taken on the mantle of surrogate father when John had been too broken up over his dead wife to even attempt to be their actual father. Sure, he was Dean's boss too, but he was family first.

He knew it would be asking a lot but if Bobby could help them out, help keep Cas from having to do such a risky job, then maybe he could enjoy what was left of his school years. His little sister would be safe from the system and just maybe...Cas might consider something more with Dean. Okay, so it was possible Dean's intentions weren't _all_ fucking selfless, he wasn't a monk – but hey, he got points for being honest with himself at least!

Although, as he pulled in to Bobby's junk littered yard that afternoon, his stomach began to writhe. He was...he was actually about to do this. About to come out to someone. Because no way would Bobby – annoyingly shrewd and observant sonofabitch that he was — no way would he _not_ figure out what had gone down once he knew Cas's profession. He'd see through Dean like tracing paper. But he didn't want to lie to Bobby, plus if he was going to help them he deserved all the facts.

And.......ah, fuck it.

Dean swung out of the car and walked up to the weathered porch, resisting the urge to barf in the open bonnet of an old Camaro on his way there. After two knocks Bobby's disgruntled face appeared from behind the door and surveyed him.

"What in the hell have you gotten yourself into now?"

"And a good afternoon to you too, you crotchety old curmudgeon," Dean fired back.

"You watch who you're calling old, boy!" he barked, but stood back to let Dean in, seemingly unbothered by Dean's other chosen descriptors. "So what brings your sorry hide to Chateau Singer? Your text worried me some." He turned, face more serious. "It ain't your daddy again, is it?"

"No, nah, we're coasting along okay at home," Dean reassured quickly. They made their way to stand in the middle of the cluttered living room.

"It's actually," he shuffled his feet a bit on the worn planks, "it's about me and a friend of mine who's in trouble."

Bobby's face turned to stone.

"What's her name and when's it due?"

"Jesus! Bobby, gimme a little credit!" Dean exclaimed. "It's nothing like that. My friend he...he's had to get into a dangerous line of work and from what I gather he's the only one taking care of the homestead. Or taking care of his baby sister either."

"Parents not in the picture?"

"Not in a good way. Pretty sure there's only one and she's drinking, smoking or injecting away all his hard earned cash."

"Mmhmm, and you know he's earnin' it at a risk?"

"Yes."

"Drugs?"

"No."

"A gang?"

"No." Dammit, Dean could feel his face heating. And suddenly he couldn't figure out where to put his hands, so he stuffed them deep in his pockets.

Bobby's brows knitted before raising slightly in understanding. Then even higher as he inferred the rest. Dean's face got hotter.

"I see." Bobby appraised him, arms folded, looking monumentally unimpressed. "And he just...told you this incredibly private, _illegal_ bit of info. 'Cause you're so close; you and this guy I never heard of before just now?"

Dean sighed. "You gonna make me say it?" Bobby already knew. Dean knew he knew. And Bobby knew that Dean knew he knew, so there was no reason to make him try to force those words out of his gullet. Dean cast a glance upwards.

"Christ alive, I knew you were an idjit but I didn't realize you'd be fool enough to fall for a workin' boy. How much is he tryin'a squeeze you for?"

"What?!" Dean flushed red hot and his head snapped back to Bobby. "He'd never– Okay, yes, I met him on the job but I'll have you know he's never accepted a _dime_ from me, and he has no idea I'm here talking to you about this. All that stuff about his sister and his mom I saw first hand."

Bobby let out an aggressive puff of breath. "Still looking for this credit I'm meant to be givin' ya, Dean. Okay, so say I believe you that he's not running a scam. If you don't need money, what do ya think I can do?"

"Well, he's still in school," here came the risky part, "my school actually, as of last week and I was thinking...you know that upstairs you never use? The one with three bedrooms and enough room for a teenager and an eight year old to comfortably stay for, say four and a half months, until that teenager becomes a legal adult...?"

"I vaguely recall..." muttered Bobby, his eyes narrowing. "And why am I not just simply calling the relevant authorities?"

"Come on Bobby, they'd be split up in a heartbeat. And god knows if they'd let Anna see Cas again if they found out what he's been doing for money. He takes such good care of her Bobby, you should see it." Dean shook his head, starting to feel slightly desperate. "He's all she's got."

Bobby simply kept up his highly skeptical squinting.

"I'd help pay their upkeep, Bobby, I swear," Dean pleaded hastily, "I'll work my shifts for free too! Just, they _need_ to get outta that house."

Bobby shook his head incredulously. "Holy hell, I gotta meet this kid. Guy's turned you into Mother frickin' Theresa." They stood there for a moment in silence.

"Bobby, _please_ ," said Dean, trying hard not to just fall to his knees and beg. Which, he realized suddenly, he would do. In a heartbeat. God damn, he had it _bad_.

"I'll meet 'im first," Bobby grunted finally. "Before I decide to do or _not_ do anything. Got it?" Dean let out a breath. It was a start.

"Yeah, I got it. Thanks, Bobby." He let his shoulders loosen a bit. Then, after another beat, "You're not...gonna say anything? About Cas being a guy?"

"What is there to say? Apart from the fact you're just damn lucky you didn't get caught soliciting, ya giant dumbass." He looked up at Dean, softening slightly, "I don't got a problem with who you like, son, and I ain't gonna judge some kid for doin' what they had'ta to survive. I am gonna judge you for walking to a street corner, don't think you've avoided that conversation by the way. But, he must really be something special, this Cas."

Dean felt a thrumming warmth towards the scruffy grouch in the trucker hat. The term 'hidden depths' never seemed more poignant than with Bobby.

"Well, I gotta get back now, start dinner," said Dean awkwardly, needing this conversation to conclude kinda now, having reached his quota in both emotional vulnerability and embarrassment. He made towards the front door, but paused with his hand on the knob, turning. "I don't want Dad to know, about u– about me. Not just yet."

"You're lucky discretion's my middle name then, huh?"

"I thought it was Mervin," snarked Dean. Bobby took a swipe at him with his hat which he dodged, laughing.

"Git along, ya idjit! And bring your boy over here in the next couple days for dinner if you can." And with that Dean was herded out the door and it slammed shut behind him.

Welp. That went a metric fuck ton better than Dean had anticipated, Christ he'd come out to someone! And they'd been totally un-fussed about it. Dean smiled to himself a fair bit on the drive back home, giddy relief mixing with a brand new set of anticipatory nerves.

Now he just had to tell Cas about his plan. Oh, that conversation was just gonna go down a treat, he could tell.

But Bobby had called Cas _his_. That he could get used to.

— – - • - – —

That evening Dean had promised to do a few chores that had been piling up, the least pleasant of which was unclogging the guttering around the back of the house. Why his dad, whose employment and therefore hours, were sporadic at best couldn't have done this while they were at school, he didn't know. Well. He did know, he just wasn't impressed by the reason.

Taking care of their home hadn't been top of John's priorities for many years. It was almost as if admitting that these were jobs he had to do alone, without the aid of their mother just opened up the wound afresh – so he didn't try. By this point Dean was so familiar with the slack that he picked up that he didn't even think on it. He'd not known that their home life could be considered unusual until he'd started spending time at friends' houses and had seen their moms doing the jobs he was so used to doing.

Their dad's work pulled him away at odd hours and, sometimes, for days at a time. To start with they'd been carted around the Midwest to where the latest job was. But once a longer stint back in Lawrence had occurred, a firm Bobby (who'd been in the Marines with John) and a pleading Dean had convinced John to keep renting the house, look for local work and if that was unavailable, get help to take care of the kids.

He'd done that....sometimes. Childcare was expensive. And Bobby was not only busy, but frequently on the wrong side of John's bad temper, so the latter would often be too stubborn and proud to ask for his help. And so, Dean had learned very, _very_ young, two things;

1: Sammy was his responsibility and his absolute top priority.

And,

2: Failing point one in any way was not an option.

Those lessons had been driven home in a hard way when he'd left Sammy alone once at one of the motels they'd temporarily inhabited and Little Sam had let a homeless guy into the room. Sure, Dean had left to find food since they'd run out and were hungry, and Sam had been fine, but that hadn't mattered to John. Dean sometimes still had nightmares about that punishment.

It wasn't all bad with his pop, though. There were some times when he was alright, he occasionally brought back bits and pieces from his work elsewhere as gifts, and he'd taken Dean out shooting when he was younger. True, Dean would've rather gone to the comic book store or arcade, but his dad had seemed in good spirits, and Dean desperately didn't want to disappoint him. It seemed like he did enough of that on a daily basis as it was.

It turned out Dean was an excellent marksman, which, internally, made him a little uncomfortable – he wasn't that keen on guns. But his father had looked _so_ fucking proud! And he'd said as much, whilst clapping Dean on the shoulder. John did not tend to say stuff like that. That trip had got the tally up to a grand total of one, and Dean was not going to risk losing it just because guns weren't his favorite thing ever.

But at home he'd become a wiz in the kitchen, and even though it was borne from necessity, he still enjoyed cooking a lot. Hearing Sammy compliment something he'd made was, like, one of the best things ever. And he'd pit his burgers against some diner's any day...except for the Roadhouse burgers. Not that his own wouldn't stand a chance; it's just that he was piss scared of Ellen, the owner, and what she might do to him if he dared challenge her cooking!

The gutters took all evening, after a considerable pause to make dinner, and by the time Dean was down off the ladder he was tired, covered in leaf debris, but had successfully staved off most of his nerves about what he'd be doing the next day.

He traipsed into the kitchen, toeing off his boots. Sam was sitting at the kitchen table writing something that looked very complicated into a large notebook. Dean leaned over his shoulder and, yep! That was an alien language. He maybe recognised a number three in there.

"Jeez, short-stack, you taking the Mensa entrance test or something?"

"It's advanced calculus. I like it."

"Nerd!" snorted Dean.

"Really?! You play Dungeons and Dragons online and I know for a fact you've still got that book on Cowboys; and you're calling _me_ a nerd?" Sam pulled a smug face. "You don't hide it as well as you think, Dean."

"Yeah, well at least I don't look like Chewbacca Junior."

"Sick burn, dude," Sam said with more sarcasm than was healthy for a fourteen year old, surely. God, fourteen already. Dean's internal gears clicked into parent mode without conscious thought.

"When's that gotta be in for?" he asked.

"Next week. I've done all my other work." Jesus, this kid.

"Then why don't you go outside and, I dunno, loiter in the park or something? Go be a teenager."

"Ugh, have you _met_ other teenagers?"

"Alright, that's it, you are too young to be this old!" So Dean slung an arm around his head and gave him the noogie to end all noogies.

"Aagh! Get off, jerk!"

Dean just laughed and continued his older brother duties until a loud voice cut through Sam's protests.

"Quit whatever you're doing that's making that damn racket!" The command controlled Dean's limbs like they were physically connected, and even Sam sat a little straighter in his chair. Instead of glowering at Dean he pulled a face in the direction their dad's voice had come from.

These days Sam was apparently taking more and more issue with their father. Dean only hoped it wore off as Sam got a bit older, he didn't fancy playing referee in that particular showdown.

"Weren't even being that noisy," grumbled Sam as he returned sullenly to his homework. Dean sighed, before gently messing his hand in Sam's brown mop of hair.

"You're the smart one, you know. I'm proud of you, Sammy, just don't forget to have fun sometimes" he said, then he swiftly headed toward the bathroom.

He wanted Sam to hear stuff like that. He _needed_ Sam to know it. But he didn't have to look him in the eye as he said it. As previously acknowledged, he'd already reached his quota on warm and mushy for the day.

— – - • - – —

"Hey, check it out!" Viktor held up his Health book, open at the page of the male reproductive system over which he'd drawn some interesting illustrations.

"Henrikson, cut it out," called Mrs Tran from the front of the classroom as the four guys around Dean chuckled at Viktor. But by this point in the day, Dean couldn't laugh along with them. He was a teensy bit worried that if he huffed his diaphragm any, he'd yack all over his textbooks.

It was last period before lunch, and then Project Find Cas and Talk would be a go. He'd wanted a cool code name, maybe Project Awesome or something, but he hadn't been able to decide on one, although if you abbreviated the long name it was ProFCaT – heh, like an actual cat professor. Professor Cat: teaching classes on how to lick your own butt.

And then Dean realized quite how dorky he was being. Maybe he was just doing it to alleviate some of his nerves – because, hot damn, was he _fucking_ nervous!

Quicker than he was ready for, the bell rang. Chairs scraped, people talked and Dean's stomach bubbled unpleasantly. Victor, Jesse and Gordon waited expectantly for him to collect his things and follow them.

"You guys go ahead," Dean said to his friends, "I got a thing to do. I'll see you next period." He wiped his sweaty palms on his jeans, wondering where he might find Cas since he never saw him in the cafeteria. He was pretty sure the guy took AP Chem, he'd seen a couple textbooks lying around Cas's room and that was one of them, so... near the science block maybe? It'd be a place to start.

Turned out, he didn't need to look.

Dean ended up bumping straight into Cas as he rounded a corner at full speed and knocked him right onto his ass.

"Shit, Cas, I'm sorry," said Dean quickly, offering his hand to the prone figure on the floor. Cas looked up at him in surprise for about a second before his eyes grew cold again. Oh, this was gonna be interesting. But he still took Dean's hand and Dean heaved him back to his feet. He didn't want to let go of that warm strong hand, but he did.

"I was actually trying to find you," Dean began and Cas shot him a quizzical head tilt.

"Why?" he asked warily.

"I wanted to talk to you about something and before you worry it's got nothing to do with the other night. Well, it sorta does but it sorta doesn't, I mean– look, could we just talk in my car? It's nothing bad I promise," he added as Cas grew more and more squinty with suspicion. "I just wanna have a bit of privacy. That okay?"

Eventually, after a long-ass stare, Cas nodded slowly, and Dean breathed a sigh of relief. He led them through the school to the student parking lot to Baby. It was probably Dean's imagination but he felt the prickle of people staring at them. Rationally, he knew they weren't. They had their own shit to do and were utterly uninterested in Dean and Cas walking; he kept up this mantra the whole way. It was a little easier to stamp down the paranoia this way, and that was progress he supposed.

Once the heavy doors of his beautiful car had slammed shut, he was suddenly faced with a cloying silence that he'd not anticipated. It caught him off guard.

Dean opened and shut his mouth stupidly a few times.

"Are you gonna talk or was I asked here just to be deprived of lunch?" Cas asked curtly.

"Uhh," Dean replied intelligently. His brain suddenly felt like a faulty engine. The nerves weren't his friends, for sure, but it could also have something to do with the vivid memories of what had been the purpose the last couple times Cas had been in his car. He shook his head, trying to clear it of super inappropriate thoughts.

"Sorry, uh...yeah, so...um. How've you been?" he finished lamely.

The eyebrow that went up on Cas's face was in danger of reaching Canada it went so far north. Dean felt Cas's stare settle on him like a weight, but not in a bad way. More like a familiar, heavy, comfy blanket. But a blanket that also made him feel horny....okay that analogy stopped working. But just– it felt good. If Dean couldn't have Cas's hands on him, then those beautiful blue eyes were the next best thing, even if they were filled with irritable suspicion.

"I'm fine," Cas said blandly, turning back to look at the dash instead of Dean.

Dean sighed, casting his eyes up to the roof. This wasn't going so great. "I wasn't blowing smoke up your ass when I said I wanted to get to know you, Cas," Dean sighed out.

"You wanna get to know me? Fine," bit out Cas impatiently, temper turning on a dime and making Dean jump slightly. "I hate spiders, mayonnaise, and mornings. I love my sister, reading and I'd get my coffee intravenously if I could. I've got a zero tolerance policy on douchebags and, as you've probably noticed, my people skills are... rusty. At best," he finished, losing a bit of steam.

"...well..." said Dean awkwardly after a beat, "...that's a start." Cas gave him a scathing look.

"Look, I got a suggestion," Dean steamrollered on, "and this suggestion might get me a slug in the jaw but I think it's worth the risk." Gross sweaty palms. Oh boy, these nerves were really kicking his ass.

"You didn't exactly put yourself in a situation easy to escape a fist coming at you," Cas muttered dryly.

"I could say the same to you."

And Dean regretted those words the moment they fell outta his stupid, stupid trap. "Shit. Forget I said that. I'm sorry. I just–" he ran his hands over his face and let out a breath. He always said the dumbest crap when he was nervous.

"I'm not used to talking about serious shit. So I'm just gonna say it; when me and Sammy, when we were younger my dad wasn't...he...we needed someone to help take care of us. And there's this guy called Bobby who – well, he's a bit rough around the edges but he's good people, an old army buddy of my dad's. He looked after us. Sometimes we'd stay with him for weeks." Dean released another breath.

"Seeing you with Anna...I gotta say it felt scary familiar. If it weren't for Bobby I might've...might've been in a similar situation to yourself a few years back. But because of him I didn't have to be. So I went to see Bobby yesterday. And I asked him whether he might have room for you and Anna to stay for a few months. He didn't promise anything but he said you guys should come over for dinner soon. Just...to meet."

There was a pressing quiet as Dean stopped talking. When he glanced over to the passenger seat Cas was staring at him with a terrifying mix of what seemed to be fury and shock, blue eyes blazing. That punch may well be heading his way soon...

"You..." but Cas couldn't seem to locate the words he was searching for and silence reigned in the car again as Dean found himself in the same boat.

"I...I don't know what to say to that, Dean," said Cas stiltedly, finally breaking the silence.

"Just say you'll think about it? Cas, your mom...you know it's not meant to be like that, right?"

There was another unbearably tense pause.

"She didn't used to be this bad," Cas began quietly. Dean turned in his seat at the change in Cas's tone, took in the almost glazed look in Cas's eyes as he spoke.

"It was pretty low level for a while, like after Dad left. I mean, it was never perfect but she had grandma, her mom, to help with us and it...it wasn't as bad. But when Gram died she just– it was like she stopped being a person.

"She definitely stopped being our mom. I don't even recognize her anymore. Anyone who can look at her own hungry, crying children and leave the house to go get wasted instead of helping them–" Cas cut off, his breath coming in short bursts as he continued to stare intently at the dash. "I shouldn't have to lie to Anna, lie right to her face and say 'Of course I know Mommy still loves you'. 'Mom's going to get better', 'Mom _cares_ '..."

Dean's heart broke for Cas. For Anna too. As off the rails as John had occasionally flown, he was never that bad. Dean always knew he cared even if he wasn't around, he still loved his boys even if he didn't say it, he didn't hate them even when he got angry. He just needed the anesthetic of booze every so often to dull the pain of Mary's loss. And Bobby had stepped in when he could. He'd never been as alone as Cas was.

"C'mon, you've got less than five months until you can become her official everything." He received a confused look through watery eyes. "Your...date of birth was next to your address on the form in your file," he admitted guiltily.

"You are one sly bastard, Dean Winchester," Cas said, shaking his head, and seeming to sag a little where he sat. His hand fell onto the seat between them. Dean became intensely aware of its proximity to his own.

"Come with me to Bobby's?" he said, gently. "Anna should come too, and Sam. We'll all have dinner and see how you feel. You can't exactly lose anything by it." Dean hoped his imploring face might help sway the verdict, he'd been told he had persuasive eyes, and he'd exploit the hell outta that now if he needed to.

Cas looked as if he was about to back out, but after a second of what seemed like a pretty tough internal battle, he simply nodded his head and said, "Okay."

Dean released a breath of relief and, as he relaxed, his right hand inched across the leather, the very edge of his pinky finger caught the tip of Cas's. It was as if an electrode had been attached to that exact point. He sensed rather than saw Cas stiffen a little. Suddenly their breathing was deafening in the cab of Baby, Dean could tell his own had sped up, could hear that Cas's had done the same.

He couldn't help but cling to the fact that Cas still hadn't removed his hand, hadn't broken the constant yet light contact. Almost subconsciously Dean's finger slid slowly over Cas's, gently caressing the skin there. He felt kinda light-headed. But hearing the small sigh that came from Cas, Dean realized exactly what he was doing.

He retracted his hand, though not quickly enough to make it obvious that he'd just had a sickening flash of conscience. Dean couldn't make a pass, godammit! Not with the help he was offering, he couldn't make it seem like the help had a price. Dean wasn't chivalrous by any means but he damn well hoped he wasn't _that_ big a creep.

He folded his hands on his lap and cleared his throat. "So...tomorrow evening," he said, trying to ignore the actual ache inside him at having to stop touching Cas, "does that– is that okay? For you and Anna?" Dean dared a look at Cas. His face was slightly pink, but he nodded before casting his big blues on Dean (who noted the blown pupils).

"But you're picking us up and driving us there," he said bluntly.

Dean snorted at the command. "Aye aye, cap'n," he chuckled. "Come on, let's go get lunch before all the food's gone."

"I brought a bag lunch."

"You can eat that in the cafeteria."

Cas looked at him warily. "You really...want to eat together?" Dean's stomach went a bit lurchy but he internally kicked down his stupid-ass paranoia.

"Yeah," he offered confidently with a smile. A beat passed, then Cas actually smiled back – and whatever people might say about them having lunch together was worth it _just_ for that.

— – - • - – —

**Author's Note:**

> A tamer chapter this time around but hopefully with enough feels for you. Don't worry, it'll heat up again soon ;). And a huge thank you to everyone who has read, left kudos, or taken the time to comment <3 Seriously, y'alls are wonderful and I appreciate every single one of you! (And, you know, congrats on your astronomic levels of patience too!)


End file.
